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investigating Sinatra’s draft record. But the letter became a self-fulfilling prophecy. The resulting investigation prompted this memo several weeks later to Assistant Director D. M. “Mickey” Ladd, head of the FBI’s Domestic Intelligence Division. The initial inquiry into Sinatra’s draft status was undertaken by the special agent in charge (SAC) for Newark, Sam K. McKee, who is reputed to have been one of the agents who gunned down Pretty Boy Floyd ten years earlier
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    February 8, 1944
Call 3:10 PM.
Transcribed— 3:25 PM.

MEMORANDUM FOR MR. LADD

RE: FRANK SINATRA
   SELECTIVE SERVICE
        When SAC, S. K. McKee of Newark called me at the above time and date I asked him whether or not he had heard any rumors to the effect that Frank Sinatra had paid $40,000 to obtain a 4-Fclassification. Mr. McKee stated that he had heard nothing to this effect.

    I asked SAC McKee to ascertain definitely whether Sinatra’s classification was 4-F and if so, to determine why he received this classification. However, I told him that it would not be necessary at this time to make a full scale investigation or to look into the charges of $40,000 being paid the examining doctors at Newark. McKee stated that he would do this immediately and advise the Bureau of the results.
    Respectfully,
    G. C. Callan
        
McKee informed headquarters of the results of his investigation several days later, first in a telephone call with one of Ladd’s underlings, Christopher Callan. McKee’s report was the first hint that Sinatra had given draft officials inconsistent statements about his medical condition. And the report was spiced up with a little sex
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    February 10, 1944

MEMORANDUM FOR MR. LADD

Re: FRANK SINATRA
   Selective Service
        SAC McKee of the Newark Office advised that Sinatra’s classification appeared to be regular and that he was disqualified because of a perforated ear drum and chronic mastoiditis and that his mental condition was one of emotional instability. McKee stated that in a prior physical examination in the fall of 1943 none of these defects were noted and that in a questionnaire dated December 17, 1940, in answer to a question as to his physical condition, Sinatranoted there were none to the best of his knowledge. He is classified 4-F as of December 11, 1943.
    McKee also said it had come to the attention of one of the Resident Agents at Hackensack, New Jersey, that Sinatra has an arrest record and thatHackensack County Jail, who furnished this information, gave the Agent a photograph of Sinatra, arrest #42799. McKee advised that Sinatra was arrested in 1938 on a charge of seduction which was dismissed and he was later arrested on a charge of adultery.
    I instructed McKee not to take any further action in this matter. He said he would submit a letter today covering the above.
    Respectfully,
    G. C. Callan
        
A more detailed letter to Hoover disclosed that at Sinatra’s induction physical, he left the chief clerk of his local draft board in Hudson County, N.J., with the impression that he knew he’d be rejected. And it detailed how many times Sinatra had denied being emotionally unstable before claiming, in December 1943, that he was
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    February 10, 1944
    Director, FBI
    Re: FRANK ALBERT SINATRA
SELECTIVE SERVICE
    Dear Sir:
        Reference is made to the telephone message from Mr. Christopher Callan at the Seat of Government on February 8, 1944 concerning the receipt by the Bureau of an anonymous letter alleging, in effect, that $40,000 had been paid to the doctors who examined FRANK ALBERT SINATRA and thereafter gave an opinion that SINATRA had a perforated eardrum and was unsuitable for military service.
    In accordance with instructions, the investigation was limited to an examination of SINATRA’s Selective Service File in order to obtain from that file certain information as set forth below. On February 9, 1944, the file was examined by Special Agentat Local Draft Board #19 for Hudson